Manufacture of monoazo-dyestuffs



Patented Jan. 3, 1933 UNITED STATES?- PATIENT oFncE BEBNHARD 310mm), 01*BASEL, swr'rzmnivn, AssIGiroRmo THE rum in. GEIGY s. A., or BASEL,SWITZERLAND I MANUFACTURE OF MONOAZO-DYESTUFiS v No Drawing. Applicationfiled October 3, 1929, Serial No. 397,159, and in France )ctob er 15,1928 I vention EwampZe 1 A diazo-solution prepared in the usual mannerfrom 18.5 kilos of ortho-aminodiphenyl ether ofthe formula isintroduced, at a temperature of 0-5, (3., into an aqueous solutioncontaining 47.3 kilos of para-toluene-sulpho-1-amino-8-naphthol- 3 6-disulphonic acid of the formula: I

0 of common salt, filtered and dried. It is a red powder which dissolvesin Water to a bluish-red solution and in concentratedamino-8-naphthol-disulphonic suphuric acid to a violet solution. It dyeswool and silk clear bluish-red shades of very good fastness to lightand'to rfulling. In

its free state the dyestuff has most probably the following formula: v Ir Instead of the ortho-amino-diphenyl ether used in the foregoingexample, there may be used anotheraryl-ether of ortho-aminophe: nol orof a'derivative thereof, for'example ortho-aminophenyl-ortho-tolyl etheror ortho aminophenyl-meta-tolyl ether, ortho-v aminoph'enyl-para-tolylether, orthoaminophenyl para chlorophenyl ether, ortho aminop-henyl.ortho chlorophenyl ortho-amino-para-chlorodiphenyl ether, or-

ether,

tho-aminophenyl-benzyl ether, 'meta-amino-,

para-cresol-benzyl ether, i-chloroiZ-amino phenyl-benzyl ether or thelike.

Instead of the para-toluenesulpholacid, there may be used any otherN-arylsulpho-lz8- aminonaphthol-disulphonic acid, for examplebenzene-sulpho-, chlorobenzene-sulpho-, nitrobenzene-sulpho-l8-a'minonaphthol-3z6-or-4: 6-disulphonic acid.

Example 2 A diazo-solution obtained in the usual manner from 23.4 kilosof4-chloro-2-aminophenyl-benzyl-ether of the formula:

mQo-om-mm order to maintain a neutral reaction.

naphthol-3:6-disulphonic acid of the formula:

OH N

\SOPOBH!) clear bluish-red shades, the dyeings on Wool being very fastto fulling and to light. In its free state'the dyestutf has mostprobably the following formula:

1 Instead of the benzyl ether of 4-chloro-2- aminophenol used in thisexample, there may be used the benzyl ether or the chlorobenzyl ether ofortho-aminoph'enol or of other de-' rivatlves of this compound; insteadof the 1 benzenesulpho 1 8 aminonaphthol 3 6 disulphonic acid there maybe used the corresponding toluene-sulpho-l 8aminonaphthol-3z6-disulphonic acid or another arylsulpho- 1 8-aminonaphthol-3 6-disulphonic acid.

Dyestuffs may be made from an arylsulpho-1 8 aminonaphthol -4:6-disulphonic acid (K acid) in a manner similar to that described in theforegoing examples. They yield red dyeings which aremore yellow thanthose of the corresponding dyestuffs from the aryl sulpho -1 8aminonaphthol 3 6 disul phonic acids.

What I claim is 1. A processfor the manufacture of monovazo-dyestuifs,consisting in coupling a diazo compound of anortho-aminophenol-ether of the following formula:

i wherein R stands for phenyl, tolyl, benzyl or halogen substitutionproducts and Y for H. Cl and CH with an N-benzene-sulphoderivative of a1-amino-8-naphthol-disulphonic acid of the formula:

/H OH N-SOr-X wherein X stands for 0 1-1 0 1-1 or (3 1-1 01.

2. A process for the manufacture of monoazo-dyestuifs, consisting incoupling a diazo compound of an ortho-aminophenol-benzylether with anN-benzene-sulpho-derivative of a 1-amino-8-naphthol-disulphonic acid ofthe formula:

/H v on N-SOz-X wherein X stands for C H ,'C H or C H Cl.

3. A process for the manufacture of monoazodyestuffs, conslsting incoupling a diazo compound of l-chloro-Q-amino-phenol-benzylether with anN-benzene-sulpho-derivative of a l-amino-8-napl1tholdisulph0nic acid ofthe formula wherein X stands for 0 1-15, C H or C H Cl.

4. A process for the manufacture of monoazo-dyestuffs, consisting incoupling a diazo compound of a phenyletherof the ortho-aminophenol witha toluene-sulpho-1.8-aminonaphthol-disulphonic acid.

5. A process for the manufacture of monoazo-dyestufls, consisting incoupling a diazo' compound of a phenylether of the orthoaminophenol witha toluene-sulpho-1.8-aminonaphthol-3.6-disulphonic acid.

6. A process for the manufacture of monoazo-dyestuffs, consisting incoupling a diazo compound of an ortho-aminophenol-benzylether with atoluene-sulpho-l.S-aminonaphthol-disulphonic acid. I

7. A process for the manufacture of monoazo-dyestufls, consisting incoupling a diazo 1" compound of 4-chloro-2-aminophenol-benzylether witha toluene-sulpho-l S-aminonaphthol-disulphonic acid. 1

8. A process for themanufacture of monoazo-dyestufis, consisting in,coupling a diazo compoundof i-chloro 2-a-mino-phenol benzylether V witha toluene-sulpho-l 8-amino-= naphthol-3 6-disulphonic acid.

9. The monoazo-dyestufi's of the formula:

wherein R stands for phenyl, tolyl, benzyl or halogen substitutionproducts, Y for H,Cl and CH and X for O H 0 H or C H Cl,

said dyestuffs dissolving in Water with red to blue-red and inconcentrated sulphuric acid With violet to blue coloration and dyeingWool and silk clear red shades Very fast to light and fulling. I

10. The monoazo-dyestulfs having the formula:

NaO S SO=Na said dyestufi dissolving in ater with red to blue red and inconcentrated sulphuric acid with blue coloration and dyeing W001 andsilk clear red shades Very fast to light and fulling.

In Witness whereof I have hereunto signed my name this 21st day ofSeptember, 1929.

BERNHABD RICHARD.

